119491-09-7Relevant articles and documents
Bioinspired nanophotosensitizers: Synthesis and characterization of porphyrin-noble metal nanoparticle conjugates
Bhaumik, Jayeeta,Gogia, Gitanjali,Kirar, Seema,Vijay, Lekshmi,Thakur, Neeraj S.,Banerjee, Uttam C.,Laha, Joydev K.
, p. 724 - 731 (2016)
A methodology to enhance biological delivery of photosensitizers by incorporating them into nanomaterials has been developed. In order to prepare photosensitizer nanoconjugates as biocompatible and selective probes, initially, bioconjugatable porphyrinic
Activated Type I and Type II Process for Two-Photon Promoted ROS Generation: The Coordinated Zn Matters
Cao, Hongzhi,Li, Dandan,Li, Shengli,Ni, Bo,Tian, Xiaohe,Tian, Yupeng,Wu, Jieying,Zhang, Chengkai,Zhang, Qiong
, p. 13671 - 13678 (2020)
The construction of novel classes of photosensitizers for efficient reactive oxygen species (ROS) generation is of great interest, yet it is a challenge. In this work, a bis(terpyridine)zinc(II) complex (namely, ZnL1) with two-photon absorption activity as an efficient ROS photogenerator was synthesized. Benefiting from the coordinated Zn, the decreased singlet-triplet energy gap favors the intersystem crossing process facilitating the singlet oxygen (1O2) generation via energy transfer. In addition, it makes the superoxide radical (O2·-) generation easier. This is an extremely rare study on two-photon excited ROS generation by activating type I and type II processes based on a cheaper and bioaccessible Zn complex.
Mechanofluorochromic properties of fluorescent molecules based on a dicyanomethylene-4: H -pyran and indole isomer containing different alkyl chains via an alkene module
Qian, Lebin,Zhou, Yibin,Liu, Miaochang,Huang, Xiaobo,Wu, Ge,Gao, Wenxia,Ding, Jinchang,Wu, Huayue
, p. 42180 - 42191 (2017)
A series of 3-, 4-, and 5-position indole-substituted dicyanomethylene-4H-pyran (I3PM, I4PM, and I5PM) derivatives with different alkyl chains were synthesized and their mechanofluorochromic (MFC) properties were investigated. Compared with the alkyl chains, the isomerization of the indole unit plays a more important role in regulating the MFC properties of these compounds. The increase of the alkyl chain length and the isomerization of the alkyl chain are favorable to the effective mechanofluorochromism of the I3PM derivatives, however, the former exhibits the opposite effect on that of the I4PM derivatives. The opposite alkyl length-dependent MFC behavior is closely related to the degree of distortion of the molecular conformation, namely the more twisted the molecular conformation, the more pronounced the MFC phenomenon. In particular, the introduction of the alkyl chains is completely detrimental to the MFC properties of the I5PM derivatives. X-Ray diffraction experiments indicate that the MFC properties of some of these compounds should be mainly attributed to the transformation from a crystalline state to an amorphous state because the weak intermolecular interactions and loose molecular packing modes in their solid-state samples can be easily damaged under external force stimuli as revealed by the single crystal X-ray diffraction analysis.
Synthesis, antimycobacterial and anticancer activity of novel indole-based thiosemicarbazones
Mashayekhi, Vida,Haj Mohammad Ebrahim Tehrani, Kamaleddin,Azerang, Parisa,Sardari, Soroush,Kobarfard, Farzad
, (2021/09/08)
Based on the structural elements of bioactive indole-based compounds, a series of novel 1-substituted indole-3-carboxaldehyde thiosemicarbazones were synthesized as potential antimycobacterial and anticancer agents. The derivatives were prepared via a two
Synthesis of 3-Formylindoles via Electrochemical Decarboxylation of Glyoxylic Acid with an Amine as a Dual Function Organocatalyst
Lin, Dian-Zhao,Huang, Jing-Mei
supporting information, p. 5862 - 5866 (2019/08/26)
A new method for 3-formalytion of indoles has been developed through electrochemical decarboxylation of glyoxylic acid with the amine as a dual function organocatalyst. The amine facilitated both the electrochemical decarboxylation and the nucleophilic reaction efficiently, whose loading can be as low as 1 mol %. This protocol has a broad range of functional group tolerance under ambient conditions. The gram-scale experiment has shown great potential in the synthetic application of this strategy.
Visible-Light-Mediated α-Oxygenation of 3-(N,N-Dimethylaminomethyl)-Indoles to Aldehydes
Stanek, Filip,Paw?owski, Robert,Mlynarski, Jacek,Stodulski, Maciej
supporting information, p. 6624 - 6628 (2018/10/20)
The visible-light-mediated oxygenation of 3-N,N-(dimethylaminomethyl)-indoles bearing various substituents afforded a series of 3-carbaindole derivatives. Herein we describe the reaction scope, a plausible mechanism and a practical application of this transformation in the formal synthesis of (–)-vincorine is described as well.
α-Arylidene Diacylglycerol-Lactones (DAG-Lactones) as Selective Ras Guanine-Releasing Protein 3 (RasGRP3) Ligands
Ann, Jihyae,Czikora, Agnes,Saini, Amandeep S.,Zhou, Xiaoling,Mitchell, Gary A.,Lewin, Nancy E.,Peach, Megan L.,Blumberg, Peter M.,Lee, Jeewoo
supporting information, p. 6261 - 6276 (2018/06/11)
Diacylglycerol-lactones have proven to be a powerful template for the design of potent ligands targeting C1 domains, the recognition motif for the cellular second messenger diacylglycerol. A major objective has been to better understand the structure activity relations distinguishing the seven families of signaling proteins that contain such domains, of which the protein kinase C (PKC) and RasGRP families are of particular interest. Here, we synthesize a series of aryl- and alkyl-substituted diacylglycerol-lactones and probe their relative selectivities for RasGRP3 versus PKC. Compound 96 showed 73-fold selectivity relative to PKCα and 45-fold selectivity relative to PKC? for in vitro binding activity. Likewise, in intact cells, compound 96 induced Ras activation, a downstream response to RasGRP stimulation, with 8-29 fold selectivity relative to PKCδ S299 phosphorylation, a measure of PKCδ stimulation.
Dicyanomethylene-4H-pyran derivatives as well as preparation method and application thereof
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Paragraph 0106; 0107; 0108; 0109; 0110; 0111; 0112, (2017/12/27)
The invention particularly relates to dicyanomethylene-4H-pyran derivatives as well as a preparation method and an application thereof. The preparation method of the dicyanomethylene-4H-pyran derivatives comprises the following steps: (1) 2,6-dimethyl-4H-pyran-4-one 1 as a starting material is subjected to an addition-elimination reaction with malononitrile, and an intermediate 2 is obtained; (2) the intermediate 2 is subjected to an addition-elimination reaction with indolal with different alkyl chains, and the dicyanomethylene-4H-pyran derivatives are obtained. Indole structural units with different alkyl groups and dicyanomethylene-4H-pyran structural units are introduced into the field of organic solid luminescent materials, novel piezoluminescence color change materials are developed, and the derivatives play an important role in the field of photoelectricity. The provided method adopts a simple synthesis process, purification is easy, and the synthesized piezoluminescence materials are quite applicable to various fields of preparation of pressure sensors, anti-counterfeiting trademarks and the like and have good scientific research value and industrialized application potential.
Synthesis and antimycobacterial activity of novel thiadiazolylhydrazones of 1-substituted indole-3-carboxaldehydes
Haj Mohammad Ebrahim Tehrani, Kamaleddin,Mashayekhi, Vida,Azerang, Parisa,Sardari, Soroush,Kobarfard, Farzad,Rostamizadeh, Kobra
, p. 224 - 236 (2014/02/14)
A series of novel thiocarbohydrazones of substituted indoles and their corresponding thiadiazole derivatives were prepared, and their structures were confirmed by different analytical and spectroscopic methods. The derivatives were prepared by a sequential synthetic strategy including substitution at N-1 position of indole ring by various aliphatic and benzylic substituents, followed by condensation with thiocarbohydrazide, and finally cyclization by triethyl orthoformate. The derivatives were tested for their antimycobacterial activity against Mycobacterium bovis BCG, and the results revealed that among the synthesized compounds, thiadiazole derivatives 4e, 4f, 4n, 4p, 4q, and 4t exhibited the highest activity with IC50 value of 3.91 μg/mL. The results indicate that the thiadiazole moiety plays a vital role in exerting antimycobacterial activity. A series of indole-based thiadiazole derivatives with various substitutions at N-1 position of indole ring have been synthesized and tested for their antimycobacterial activity. Compounds 4e (R = butyl), 4f (R = pentyl), 4n (R = 4-fluorobenzyl), 4p (R = 4-chlorobenzyl), 4q (R = 4-bromobenzyl) and 4t (R = 4-methoxybenzyl) were the most potent derivatives with IC50 value of 3.91 μg/mL.
